JPH11322721A - 環式４―オキソアミジンの製造方法 - Google Patents

環式４―オキソアミジンの製造方法

Info

Publication number: JPH11322721A
Authority: JP; Japan
Prior art keywords: compound; group; halogen; cyclic; general formula
Prior art date: 1998-03-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP11081939A

Other languages

English (en)

Japanese (ja)

Inventor

Karlheinz Drauz

ドラウツカールハインツ

Rolf Dr Hoffmann

ホフマンロルフ

Ivan Pelgrims

ペルグリムスイヴァン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Degussa GmbH

Degussa Huels AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-03-27

Filing date

1999-03-25

Publication date

1999-11-24

1999-03-25 Application filed by Degussa GmbH, Degussa Huels AG filed Critical Degussa GmbH

1999-11-24 Publication of JPH11322721A publication Critical patent/JPH11322721A/ja

Status Pending legal-status Critical Current

Links

125000004122 cyclic group Chemical group 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 11
230000003647 oxidation Effects 0.000 claims abstract description 9
238000007254 oxidation reaction Methods 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 7
150000001923 cyclic compounds Chemical class 0.000 claims abstract description 5
229910052763 palladium Inorganic materials 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
150000001299 aldehydes Chemical class 0.000 claims abstract description 4
150000002576 ketones Chemical class 0.000 claims abstract description 4
230000001590 oxidative effect Effects 0.000 claims abstract description 4
239000007800 oxidant agent Substances 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 30
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 15
-1 furfuryl Chemical group 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
235000008206 alpha-amino acids Nutrition 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229910052741 iridium Inorganic materials 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
239000003791 organic solvent mixture Substances 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 abstract description 3
239000013543 active substance Substances 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract description 2
239000003960 organic solvent Substances 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
239000011877 solvent mixture Substances 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
IWKWOYOVCXHXSS-UHFFFAOYSA-N 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound O=C1NC(CCCC)=NC11CCCC1 IWKWOYOVCXHXSS-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 5
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
YGVGITVCEHRBDK-UHFFFAOYSA-N 1-aminocyclopentane-1-carboxamide Chemical compound NC(=O)C1(N)CCCC1 YGVGITVCEHRBDK-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
CZSZQIRYTFUSKQ-UHFFFAOYSA-N 2-butyl-1,3-diazaspiro[4.4]nonan-4-one Chemical compound N1C(CCCC)NC(=O)C11CCCC1 CZSZQIRYTFUSKQ-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001409 amidines Chemical class 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
125000004437 phosphorous atom Chemical group 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000005219 aminonitrile group Chemical group 0.000 description 2
PQRDTUFVDILINV-UHFFFAOYSA-N bcdmh Chemical compound CC1(C)N(Cl)C(=O)N(Br)C1=O PQRDTUFVDILINV-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
KFPMRYNOEZCHDP-UHFFFAOYSA-N 1-aminocyclopentane-1-carbonitrile Chemical compound N#CC1(N)CCCC1 KFPMRYNOEZCHDP-UHFFFAOYSA-N 0.000 description 1
YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical compound CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 description 1
QBYVXZFKAFQFKU-UHFFFAOYSA-N 2-butyl-5-methyl-5-propylimidazolidin-4-one Chemical compound CCCCC1NC(=O)C(C)(CCC)N1 QBYVXZFKAFQFKU-UHFFFAOYSA-N 0.000 description 1
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229940123413 Angiotensin II antagonist Drugs 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
238000007059 Strecker synthesis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000007854 aminals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910001919 chlorite Inorganic materials 0.000 description 1
229910052619 chlorite group Inorganic materials 0.000 description 1
QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000006056 electrooxidation reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
229960002198 irbesartan Drugs 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
QRYJGVNQNLCGGZ-UHFFFAOYSA-N spiro[4.4]nonan-4-one Chemical compound O=C1CCCC11CCCC1 QRYJGVNQNLCGGZ-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP11081939A 1998-03-27 1999-03-25 環式４―オキソアミジンの製造方法 Pending JPH11322721A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19813435.5		1998-03-27
DE19813435		1998-03-27

Publications (1)

Publication Number	Publication Date
JPH11322721A true JPH11322721A (ja)	1999-11-24

Family

ID=7862474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11081939A Pending JPH11322721A (ja)	1998-03-27	1999-03-25	環式４―オキソアミジンの製造方法

Country Status (5)

Country	Link
US (1)	US6037474A (de)
EP (1)	EP0945441A3 (de)
JP (1)	JPH11322721A (de)
CA (1)	CA2267080A1 (de)
DE (1)	DE19912383A1 (de)

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HU218680B (hu) *	1997-07-25	2000-10-30	Sanofi-Synthelabo	Eljárás 1,3-diaza-spiro[4,4]non-1-én-4-on-származékok előállítására és 1-ciano-1-(acil-amino)-ciklopentán intermedierek
US7023345B2 (en) *	2004-05-03	2006-04-04	Sensormatic Electronics Corporation	Enhancing magneto-impedance modulation using magnetomechanical resonance
GB2420214A (en)	2004-11-12	2006-05-17	Daniel Grant	A conveyor system incoprorating display means
US8168667B2 (en)	2006-05-31	2012-05-01	Galapagos Nv	Imidazolidine derivatives, uses therefor, preparation thereof and compositions comprising such
EP2152673B1 (de) *	2007-05-22	2014-08-20	Firmenich S.A.	3- bis 7-gliedrige 1,3-diaza-4-oxo-heterocyclische derivate zur freisetzung von aktive aldehyde oder ketone
GB2463514C (en)	2008-09-11	2018-09-26	Galapagos Nv	Imidazolidine compounds and uses therefor
CZ302407B6 (cs) *	2009-03-12	2011-05-04	Univerzita Pardubice	Zpusob prípravy 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-onu
US8940742B2 (en)	2012-04-10	2015-01-27	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
US9751888B2 (en)	2013-10-04	2017-09-05	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
PT3052485T (pt)	2013-10-04	2021-10-22	Infinity Pharmaceuticals Inc	Compostos heterocíclicos e suas utilizações
MX382033B (es)	2014-03-19	2025-03-13	Infinity Pharmaceuticals Inc	Compuestos heterocíclicos para utilizarlos en el tratamiento de trastornos mediados por pi3k-gamma.
WO2016054491A1 (en)	2014-10-03	2016-04-07	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
WO2017048702A1 (en)	2015-09-14	2017-03-23	Infinity Pharmaceuticals, Inc.	Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same
WO2017161116A1 (en)	2016-03-17	2017-09-21	Infinity Pharmaceuticals, Inc.	Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors
WO2017214269A1 (en)	2016-06-08	2017-12-14	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
CN108976170B (zh) *	2018-08-14	2022-04-22	华南理工大学	一种5-三氟甲基-4h-咪唑啉-4-酮衍生物及合成方法
CN119874677B (zh) *	2025-03-26	2025-06-13	四川大学	咪唑烷酮类化合物、多孔有机聚合物凝胶及其制备方法和应用

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1999
- 1999-03-19 EP EP99105642A patent/EP0945441A3/de not_active Withdrawn
- 1999-03-19 DE DE19912383A patent/DE19912383A1/de not_active Withdrawn
- 1999-03-25 JP JP11081939A patent/JPH11322721A/ja active Pending
- 1999-03-25 US US09/276,345 patent/US6037474A/en not_active Expired - Fee Related
- 1999-03-26 CA CA002267080A patent/CA2267080A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CA2267080A1 (en)	1999-09-27
DE19912383A1 (de)	1999-09-30
EP0945441A3 (de)	2002-07-17
US6037474A (en)	2000-03-14
EP0945441A2 (de)	1999-09-29

Publication	Publication Date	Title
JPH11322721A (ja)	1999-11-24	環式４―オキソアミジンの製造方法
CN1926102B (zh)	2011-01-05	N-保护的4-酮脯氨酸衍生物的制备方法
KR20020022688A (ko)	2002-03-27	티아졸리딘의 제조 방법
EP2397141A1 (de)	2011-12-21	Verfahren zur Synthese von Beta-Aminosäuren und Derivaten daraus
JP2004502678A (ja)	2004-01-29	４−アルコキシシクロヘキサン−１−アミノカルボン酸エステル及びその製造法
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US8519168B2 (en)	2013-08-27	Process and intermediates for the synthesis of 1,2-substituted 3,4-dioxo-1-cyclobutene compounds
IL116384A (en)	1996-10-16	Ylidene compounds and their preparation
JP2008546642A (ja)	2008-12-25	置換テトラフルオロベンジルアニリン化合物、及びその薬学的に許容される塩の製造方法
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CA2252344C (en)	2002-12-10	Improved methods of preparing 4-cyano-4-(substituted indazole)cyclohexane-carboxylic acids useful as pde4 inhibitors
RU2156238C2 (ru)	2000-09-20	Способ получения диоксоазабициклогексанов
JPH05503718A (ja)	1993-06-17	光学異性ヒダントインの分割方法
JP2771257B2 (ja)	1998-07-02	イミダゾール誘導体の製法
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JPS63166868A (ja)	1988-07-11	（ｒ）−または（ｓ）−５−イミダゾリルメチル−３−置換ヒダントイン
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JPH03287567A (ja)	1991-12-18	光学活性四級アンモニウム塩の製造法
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